I wrapped @smileyborg's iOS7 solution in a category

In the interest of separating concerns I decided to wrap this clever solution by @smileyborg into a UICollectionViewCell+AutoLayoutDynamicHeightCalculation category.

The category also rectifies the issues outlined in @wildmonkey's answer (loading a cell from a nib and systemLayoutSizeFittingSize: returning CGRectZero)

It doesn't take into account any caching but suits my needs right now. Feel free to copy, paste and hack at it.

UICollectionViewCell+AutoLayoutDynamicHeightCalculation.h

#import <UIKit/UIKit.h>

typedef void (^UICollectionViewCellAutoLayoutRenderBlock)(void);

/**
 *  A category on UICollectionViewCell to aid calculating dynamic heights based on AutoLayout contraints.
 *
 *  Many thanks to @smileyborg and @wildmonkey
 *
 *  @see stackoverflow.com/questions/18746929/using-auto-layout-in-uitableview-for-dynamic-cell-layouts-variable-row-heights
 */
@interface UICollectionViewCell (AutoLayoutDynamicHeightCalculation)

/**
 *  Grab an instance of the receiving type to use in order to calculate AutoLayout contraint driven dynamic height. The method pulls the cell from a nib file and moves any Interface Builder defined contrainsts to the content view.
 *
 *  @param name Name of the nib file.
 *
 *  @return collection view cell for using to calculate content based height
 */
+ (instancetype)heightCalculationCellFromNibWithName:(NSString *)name;

/**
 *  Returns the height of the receiver after rendering with your model data and applying an AutoLayout pass
 *
 *  @param block Render the model data to your UI elements in this block
 *
 *  @return Calculated constraint derived height
 */
- (CGFloat)heightAfterAutoLayoutPassAndRenderingWithBlock:(UICollectionViewCellAutoLayoutRenderBlock)block collectionViewWidth:(CGFloat)width;

/**
 *  Directly calls `heightAfterAutoLayoutPassAndRenderingWithBlock:collectionViewWidth` assuming a collection view width spanning the [UIScreen mainScreen] bounds
 */
- (CGFloat)heightAfterAutoLayoutPassAndRenderingWithBlock:(UICollectionViewCellAutoLayoutRenderBlock)block;

@end

UICollectionViewCell+AutoLayoutDynamicHeightCalculation.m

#import "UICollectionViewCell+AutoLayout.h"

@implementation UICollectionViewCell (AutoLayout)

#pragma mark Dummy Cell Generator

+ (instancetype)heightCalculationCellFromNibWithName:(NSString *)name
{
    UICollectionViewCell *heightCalculationCell = [[[NSBundle mainBundle] loadNibNamed:name owner:self options:nil] lastObject];
    [heightCalculationCell moveInterfaceBuilderLayoutConstraintsToContentView];
    return heightCalculationCell;
}

#pragma mark Moving Constraints

- (void)moveInterfaceBuilderLayoutConstraintsToContentView
{
    [self.constraints enumerateObjectsUsingBlock:^(NSLayoutConstraint *constraint, NSUInteger idx, BOOL *stop) {
        [self removeConstraint:constraint];
        id firstItem = constraint.firstItem == self ? self.contentView : constraint.firstItem;
        id secondItem = constraint.secondItem == self ? self.contentView : constraint.secondItem;
        [self.contentView addConstraint:[NSLayoutConstraint constraintWithItem:firstItem
                                                                     attribute:constraint.firstAttribute
                                                                     relatedBy:constraint.relation
                                                                        toItem:secondItem
                                                                     attribute:constraint.secondAttribute
                                                                    multiplier:constraint.multiplier
                                                                      constant:constraint.constant]];
    }];
}

#pragma mark Height

- (CGFloat)heightAfterAutoLayoutPassAndRenderingWithBlock:(UICollectionViewCellAutoLayoutRenderBlock)block
{
    return [self heightAfterAutoLayoutPassAndRenderingWithBlock:block
                                            collectionViewWidth:CGRectGetWidth([[UIScreen mainScreen] bounds])];
}

- (CGFloat)heightAfterAutoLayoutPassAndRenderingWithBlock:(UICollectionViewCellAutoLayoutRenderBlock)block collectionViewWidth:(CGFloat)width
{
    NSParameterAssert(block);
    
    block();
    
    [self setNeedsUpdateConstraints];
    [self updateConstraintsIfNeeded];
    
    self.bounds = CGRectMake(0.0f, 0.0f, width, CGRectGetHeight(self.bounds));
    
    [self setNeedsLayout];
    [self layoutIfNeeded];
    
    CGSize calculatedSize = [self.contentView systemLayoutSizeFittingSize:UILayoutFittingCompressedSize];
    
    return calculatedSize.height;
    
}

@end

Usage example:

- (CGSize)collectionView:(UICollectionView *)collectionView layout:(UICollectionViewLayout *)collectionViewLayout sizeForItemAtIndexPath:(NSIndexPath *)indexPath
{
    MYSweetCell *cell = [MYSweetCell heightCalculationCellFromNibWithName:NSStringFromClass([MYSweetCell class])];
    CGFloat height = [cell heightAfterAutoLayoutPassAndRenderingWithBlock:^{
        [(id<MYSweetCellRenderProtocol>)cell renderWithModel:someModel];
    }];
    return CGSizeMake(CGRectGetWidth(self.collectionView.bounds), height);
}

Thankfully we won't have to do this jazz in iOS8, but there it is for now!